This invention relates to benzodioxolesulfonamides and benzodioxansulfonamides which are useful as plant growth regulants and in particular as herbicides.
Chem. Ber., 105, 2791 (1972) describes the preparation of N-butylcarbamoyl-p-toluenesulfamate, but does not claim utility as a pesticide: ##STR1##
German Pat. No. 940,292 describes the preparation of N-[arylcarbamoyl]arylsulfamides and claims utility as textile assistants, pharmaceuticals and pesticides: ##STR2## wherein each of X and X.sup.1 is H, or each is ethoxy.
Netherlands Patent No. 121,788, published Sept. 15, 1966, teaches the preparation of compounds of Formula (i), and their use as general or selective herbicides: ##STR3## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 W.sub.1 is O, S, SO or SO.sub.2 ; PA1 R.sub.1 is H or CH.sub.3 ; PA1 R.sub.2 is H or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are independently H or CH.sub.3 ; PA1 A is ##STR9## X is CH.sub.3, OCH.sub.3, or Cl; Y is C.sub.2 H.sub.5, CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NH.sub.2, NHCH.sub.3, SCH.sub.3, N(CH.sub.3).sub.2, CH(OCH.sub.3).sub.2 or ##STR10## Z is CH or N; X.sub.1 is CH.sub.3 or OCH.sub.3 ; PA1 G is O or CH.sub.2 ; PA1 X.sub.2 is C.sub.1 -C.sub.3 alkyl or CH.sub.2 CF.sub.3 ; and PA1 Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3 or SC.sub.2 H.sub.5 ; PA1 (1) Compounds of Formula I where W and W.sub.1 have identical values. PA1 (2) Compounds of Formula II where W and W.sub.1 have identical values. PA1 (3) Compounds of Preferred 1 where A is ##STR11## and R.sub.7 is H. (4) Compounds of Preferred 2 where A is ##STR12## and R.sub.7 is H. (5) Compounds of Preferred 3 where R.sub.2 is H or CH.sub.3. PA1 (6) Compounds of Preferred 5 where Y is CH.sub.3 or OCH.sub.3. PA1 (7) Compounds of Preferred 6 where W and W.sub.1 are O or S. PA1 (8) Compounds of Preferred 6 where W and W.sub.1 are SO or SO.sub.2. PA1 Y.sub.3 is C.sub.1 -C.sub.2 alkoxy.
French Patent No. 1,468,747 discloses the following para-substituted phenylsulfonamides, useful as antidiabetic agents: ##STR4## wherein R=H, halogen, CF.sub.3 or alkyl.
Logemann et al., Chem. Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR5## wherein R is butyl, phenyl or ##STR6## and R.sub.1 is hydrogen or methyl.
When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR7## Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound.
Undesired vegetation can cause substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, soybean and the like.
Although a wide variety of materials are available which can be used for killing or inhibiting (controlling) the growth of undesired vegetation the need exists for still more effective herbicides that destroy or control weeds without causing significant damage to useful crops.